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0:46

Hey, everybody, thank you so much for joining

0:48

us again on these Thursday speaker series

0:50

that we've been doing. This is very honestly

0:54

my favorite thirty minutes in the week when

0:56

I get to take a break and talk to people

0:58

that I either really admire in the industry and

1:00

sometimes our friends of mine too, and today

1:02

is definitely both of those. Today is a

1:05

very cool session for me personally. I

1:07

get to talk to two friends of mine, but also

1:09

just two creators that I think are at

1:11

the top of their game in podcasting

1:14

and comedy. We launched a show

1:16

before we were part of iHeartRadio.

1:19

We were a company called Stuff Media and

1:21

we've been building a podcast network for

1:23

almost ten years. And one

1:25

of the shows we launched, one of the last shows

1:27

we actually launched before getting acquired

1:29

by iHeartRadio to become the

1:32

iHeartRadio podcast division, was

1:34

a show called The Daily Zeitgeist, and

1:36

today we have two hosts from that show,

1:38

Jack O'Brien and Miles Gray joining

1:41

us.

1:41

Jack.

1:42

Miles, first of all, I know you guys are slammed

1:44

for reasons that we will get into as we talk about

1:46

what you do with your days and weeks, But first of all,

1:48

just thank you so much for joining today.

1:50

It really doesn't mean a lot to me.

1:52

Thanks for having me, us for having

1:54

us.

1:54

Jack, I'll start with you, so like, I think one of the coolest

1:56

things about podcasting is that it's still

1:59

a relative, simply new medium,

2:01

and anybody in this medium didn't

2:04

start out as a podcaster. They were

2:06

doing something before they were doing podcasting.

2:09

I think that keeps it really interesting.

2:10

We all have sort of diverse backstories, and

2:12

we bring a lot of other industries to the table,

2:15

whether it's TV or film or print or whatever

2:17

the case may be. So, Jack, what were

2:19

you doing before you were doing

2:21

podcasting full time?

2:23

Sure, I started a website like

2:25

a decade ago or more called

2:27

crack dot com. It was just like a humor

2:30

website. I was just out of college, and

2:32

we kind of steadily grew that over the course

2:34

of a decade to be a pretty massive

2:37

humor site. But there were just some things

2:40

about the online publishing,

2:42

whether it be articles or videos,

2:44

that were becoming more and more frustrating.

2:47

You know, we were more and more reliant.

2:48

On social media to get our

2:50

content distributed, and social

2:53

media was more and more willing to

2:55

throttle your content, just depending

2:57

on how much you pay it. Meanwhile, I had also

2:59

long a podcast for

3:01

that website that I hosted called the Cracked

3:04

Podcast and very creatively titled.

3:06

That was just the most fun part of my job.

3:08

I loved podcasting. I loved the

3:10

direct access that it gave me to our

3:13

audience. It also kind of gave a

3:15

look behind the scenes because I would just take

3:17

the most interesting conversations from our

3:20

editorial room and like bring them

3:22

to our audience, and

3:24

I just felt like there was a huge opportunity

3:27

there. And also it was just the type

3:29

of content I was consuming more than

3:32

any other type of content, and it just

3:34

seemed like it was kind of circumvented

3:36

some of those issues we were having in the online

3:39

publishing space, whether it be video

3:41

or written stuff, because there's

3:44

so many different paths in

3:46

podcasting to reach an audience,

3:48

so you get directly plugged into the

3:50

people you're trying to reach.

3:52

Very cool Miles.

3:53

What about you, man, what were you doing before being a podcast

3:55

full time?

3:56

Before that?

3:57

I mean going starting way back,

4:00

used to work in politics as a political consultant

4:02

lobbyist for a number of years. Got fully

4:05

disillusioned by that, so I went

4:07

into comedy my first love, and from

4:09

there I just basically was like any

4:11

comedian trying to become an improviser

4:13

who got on the office or parks and rec Eventually,

4:16

once that path dried out a bit, I started

4:18

sort of making viral video and viral content

4:21

for different companies.

4:23

So first started working for a radio station.

4:25

In LA, then worked for YouTube,

4:27

then Playboy, then Conde Nast

4:29

Entertainment was where I was right before

4:32

coming to the stuff media slash

4:34

iHeart Network, where I was directing and

4:37

developing like video series for Condye nast

4:39

entertainment. So I've always kind of had

4:41

my hands in the content

4:43

space. But I think like everything, like

4:45

I was there the beginning of digital video

4:48

and then sort of like rowed that out to like the top

4:50

point, and podcasting

4:52

was just something that I was always consuming in the background

4:55

in my day to day.

4:55

I was always making.

4:56

Things for other people or other brands,

4:58

and it felt, like, you know, podcasting was just so

5:01

appealing because it feels like it's one of those

5:03

places where the creators fully in control of what they

5:05

make. So it was an anticipated switch that

5:07

I made, and I haven't regretted it since It's.

5:09

Pretty awesome to be able to sit in a

5:11

room and then this is a pretty good example of it,

5:13

like just the array of experiences that people

5:15

bring to this medium, the jobs they had

5:18

before this medium. When you guys rattle off

5:20

all the stuff you were doing, from political consultation

5:22

to being you know, a member of a founding team

5:24

of a pretty big website, that I

5:27

think feeds all the creative

5:29

muscle of this industry right now.

5:31

Is when you're in a room with.

5:32

The executives who are leading it in green lighting

5:34

shows and developing shows, they're bringing a

5:36

lot of other experience to the table. So

5:39

the daily zeitgeist, you guys developed

5:41

this idea. This has quietly

5:44

built an insane super fan

5:46

base of listeners. And it's not even some

5:48

niche anymore. You're several million

5:50

downloads a month on this show that started

5:52

out as a comedic take on pop

5:55

culture and the news cycle. Maybe

5:57

I'll let you guys explain it better than me, But now

5:59

I think is evolved into something a little more, maybe

6:01

even more important than maybe even

6:03

you even thought to begin with. But we'll get into that.

6:06

Where did the idea come from Jack to start

6:08

with? Like, how did you guys sit down and say, should

6:10

probably do a show? This is the conceit

6:12

this is the format, this is what we wanted to

6:15

be a not be Just.

6:16

Walk us through that cycle a little bit.

6:17

So, like I said, I podcasting was

6:20

the way I was consuming most content

6:22

at the time that I came over, and this

6:25

was just a show that I wanted to

6:27

exist that didn't exist at the time.

6:30

I found myself refreshing my feed

6:32

to like get the latest political podcasts

6:35

and pop culture podcast and there

6:37

wasn't a show that was daily that

6:39

kind of brought them all together and

6:41

gave you kind of a survey of

6:43

everything that was going on, and then I've always

6:46

just been passionate about sort of wedding

6:48

high and low culture. To Miles's point about

6:50

ninety day Fiance, I think his being

6:53

in touch with that part of the zeitgeist

6:55

brings a lot of insight to

6:57

our show. Yesterday we had to really in

6:59

depth conversation on the show about

7:01

the insights that you can glean into our

7:04

political moment based on what's happening

7:06

in The Bachelor at any given time, And

7:08

like that I think is the sweet spot for the show

7:11

because it's taking what is

7:13

happening in sort of our collective

7:15

consciousness and tying it to you

7:18

know, the political moment and you know, some

7:20

things that aren't always super fun to talk

7:22

about, but giving people an opportunity to

7:24

experience and stay up on those not

7:26

fun things in a way that keeps you feeling

7:29

a lot.

7:29

And Miles, why did you hear about

7:31

this and say I want in that's the thing

7:34

I want to put a lot of my time

7:36

against.

7:36

That's exactly it what you drew to it.

7:38

You know, like I was saying before I was a condie

7:41

nast and I was having a great

7:43

time, like making series

7:45

like Google Auto Complete

7:47

and like Accent Critique and a lot of the.

7:49

Stuff that got a lot of views over there.

7:51

But given the background of what

7:54

was happening, I felt

7:56

that I had something more to offer aside from

7:58

just developing and directing little video

8:00

content.

8:01

I felt that I had a perspective that was

8:03

pretty.

8:04

Unique in that, you know, I've had my hands

8:06

in the machine politically from

8:08

about two thousand and nine, and you

8:10

know, got into it very idealistically

8:13

when Obama was running for president, and

8:15

then sort of once I began to see

8:17

for what it was, I you know, my

8:20

sort of perspective changed, and you

8:22

know, Jack was asking all kinds

8:24

of people to gauge their interest to see who would

8:26

be like a good co host. But I just felt

8:29

having my feet in many different ponds and

8:31

working in different industries, it was like a really

8:33

good fit.

8:34

And again, like I was saying, it offered me.

8:36

A moment to have a voice, really,

8:38

and I never really even thought of myself as

8:40

someone who was going to have a podcast or someone who

8:42

would get into that.

8:43

In my mind, I was like, yeah.

8:44

I'll probably run a digital department

8:47

doing video and.

8:47

Stuff like that.

8:48

But just the second Jack even asked me, like,

8:50

all these things clicked in my mind, and I was like absolutely,

8:54

Actually, I think this is the exact

8:56

intersection of every job

8:58

and experience I've had that I can use

9:00

to really offer listeners something that

9:03

will keep them engaged. And with my background

9:05

in political organizing, I realize, you know,

9:07

apathy is such a huge thing you have to fight

9:09

against when you want people to be politically engaged

9:11

or to.

9:12

Be engaged at all.

9:13

And this just felt like, Oh, it's just a great

9:15

opportunity where it's like, we're going to give

9:17

you stuff that is really meaningful, but

9:20

you know, do it in a way that feels conversational

9:22

and accessible without just taking all the doom

9:24

in from it.

9:43

You guys have launched an incredible show

9:46

with a big fan base now, but you

9:48

are not just quote unquote podcast

9:50

hosts, right like you actually are part of the leadership

9:53

team that runs the iHeartRadio

9:55

podcast networks La Studio, and

9:58

out of that studio we produce a ton

10:00

of stuff, right, So Will Ferrell's entire

10:02

slate of shows, shondaland Audio

10:04

produces most of their stuff out of there. Shonda Rhimes's

10:07

slate of shows Chelsea Handler. The

10:09

list goes on and on. So Jack like,

10:12

it's one thing to jump in and say, I want to do a podcast.

10:15

I have a very clear idea what it is and

10:17

what it should be about.

10:17

It not about. But now you're executive producing

10:20

a slate of.

10:20

Shows with truly some

10:23

of the biggest creators of our

10:25

lives from any medium.

10:27

What is that?

10:28

Like?

10:28

How do you shepherd somebody into this medium,

10:30

like a Will Ferrell who wants to bring this like

10:32

conic ip Ron Burgundy.

10:34

How does that go?

10:36

Yeah? Fortunately, the thing that's

10:38

great about podcasting is giving these

10:40

incredibly talented people direct

10:42

access to their audience without

10:45

a whole lot of mediation, even

10:47

without a lot of cuts. You're just letting

10:49

people hear what it's really like to be

10:51

in a room with Ron Burgundy

10:54

in some cases. But Chelsea Handler,

10:56

the Workaholics podcast, you know that

10:58

was one of my favorite shows.

11:00

Colin.

11:00

I know you really liked it. It was on

11:02

Comedy Central for seven seasons. But you

11:05

know, we had one meeting with these guys

11:07

and we were like, Oh, that show

11:09

might as well have been a reality show. Like

11:11

they are their characters, the jokes

11:14

that like they come up with organically

11:17

are the same like level of jokes that

11:19

like you were seeing on the show. They were actually

11:21

living in the Rundown house

11:24

that they shot that show in, So

11:26

it was just we just got so

11:28

excited to be able to put

11:30

that in front of audiences and like,

11:33

let the magic that is those guys being

11:35

in a room together just free

11:37

and yeah, so I mean a lot of it

11:39

is super surreal. I can still

11:41

remember like going to Anchorman

11:44

in movie theaters and just having my

11:47

world changed by just like

11:49

how brilliant that was. So like being

11:51

in a room with Will is unbelievable.

11:54

But fortunately, because of this industry,

11:56

it's really easy to just tee them

11:59

up and tee their team. A lot of these folks

12:01

just have these ecosystems around

12:03

them of people who are

12:05

so good at the thing they're good at,

12:08

and so good at highlighting the

12:10

thing that they're good at. It's pretty easy

12:12

in the podcast space to tee those folks

12:14

up and just let them do what they do.

12:16

Miles, what's that moment like for you?

12:18

And like you're brainstorming an

12:20

episode a moment of bet a shtick with

12:23

a guy like Will Ferrell, and it's weird

12:25

because you're probably there, like dude

12:27

is a comedic hero of mine, but in that moment,

12:29

you're the authority because you know podcasting

12:32

better than Will Ferrell does, Like what's that like?

12:34

It was one of those moments I remember.

12:37

It was like, within a year and a half of me

12:39

leaving my job, if you had told me when

12:41

I had left to start working

12:43

in podcasting just very narrowly to

12:45

work on Daily Zeitgeist and said you

12:47

will be giving notes to Will Ferrell and you will actually

12:50

be punching up some of his jokes and

12:52

he will say I like that and

12:55

incorporated into a show. There's no way

12:57

I could. I saw no way to get there.

12:59

But that's shows you how immediately

13:02

things have changed so quickly, and like the

13:04

amount of talent that's getting into the industry.

13:06

It really is surreal.

13:07

And it was actually one of the greatest moments I think

13:09

I've had. Is like one of the most validating moments

13:11

I've had where you're kind of reading a script

13:13

and you're like, uh, I think this joke could be

13:15

better, But who am I to tell Will.

13:17

Ferrell about this?

13:18

But he's such a great collaborator

13:21

that he'll stop and say, I think

13:23

maybe this could be better.

13:23

What do you guys think?

13:24

And he opens up the discussion

13:26

for that and it allows for I think

13:29

that's truly like what makes this all work

13:31

really well is that it's collaborative and

13:33

we're allowing a lot of these creators to do a

13:35

thing that they actually themselves don't get to do a lot

13:37

because even for Will or the workaholics

13:39

guys, there's standards and practices,

13:41

there's like legal stuff that goes to where sometimes

13:44

they might not be able to have a topic

13:46

or a joke. Not that necessarily that they're controversial,

13:48

but there are other stakeholders that have input,

13:51

and I think that's what is also really attractive,

13:53

Especially for a lot of these creators.

13:54

It's like I'm everything.

13:56

I'm the executive producer, I'm the show around,

13:58

the writer or I can call those shots. So

14:00

it allows for like really a new dimension

14:02

of their creativity to come out.

14:04

And it's just a blessing to.

14:05

Be there and yeah, with our knowledge

14:07

and trust to be able to you know, participate

14:09

in that process is unbelievable.

14:11

That makes a lot of sense to me.

14:12

I want to talk real quick before we wrap

14:14

about the brand's side of this.

14:17

To switch gears for a second.

14:18

I think that as podcasting hits one hundred

14:20

million people in the country now listening to

14:22

podcasts every month, it's also the best

14:24

ad product out there.

14:26

And I think you.

14:26

Spoke to that a little bit, Miles when you

14:28

say, like, look, when creators come in, they realize

14:30

they can own the whole experience, and that is different

14:33

and cool. And I impress this upon

14:35

new brands who're thinking about podcasting

14:38

every day. The ad load is light

14:40

and we can define it. Hosts will

14:42

tell your message to their super fans.

14:44

It is the single best ad product

14:46

in media right now. Maybe just talk

14:48

about that for a second, like, Miles, from a creator's

14:51

perspective, right, Like, it's one thing to make

14:53

a great show, and you guys do, but is

14:55

you being a part of and.

14:57

Controlling to some extent the ads as

14:59

well? Is that really meaningful to you?

15:01

And maybe talk about a good experience you

15:04

had.

15:04

Absolutely.

15:05

I mean I think you know, I used to make branded

15:07

video content before and it would

15:09

be very stale, Like I'd watch it and be

15:11

like, man, I get that this X company

15:14

put a lot of money into this branded video,

15:16

but someone as a viewer is going to be like, this is

15:18

a branded video and I'm going to check

15:20

out. So when the opportunity came for us

15:22

to do ads or like, you know, like any podcast

15:24

you need to do ads, and you kind of get like you're

15:26

talking points and like there's no script that I have to

15:28

read verbatim. They're like, no, they want you

15:30

to express yourself. I'm like, that's perfect

15:33

because my personality isn't going

15:35

to try and persuade someone that I

15:37

believe in a product by saying like and it has

15:39

been verified four out of five researchers

15:42

like.

15:42

No, I'm going to say, oh my wait, hold on, how

15:44

are you guys sleeping? What kind of better you want? Okay,

15:46

let me.

15:47

Tell you about this thing I have because my back

15:49

hurts in this very specific place, Like I

15:51

want to be able to talk like I'm talking

15:53

to somebody because I'm very much like an advocate

15:55

for things that I love to people like early

15:58

adopter and things like that. So I'm always screaming

16:00

from like the mountaintops about stuff I love.

16:02

So I think a great experience I had personally

16:04

was when Mazda wanted to do something with

16:07

us.

16:07

I drive a Mazda, so it was

16:09

a no brain. I love Mazda Cars.

16:11

I just feel like I was like, I'm a fan,

16:13

so naturally I'm going

16:16

to have a different connection with it because

16:18

I really believe in it and it's

16:20

a product I actually use. So I think that's really

16:23

like the X factor in it is that it allows

16:25

a for a creator to actually

16:27

sincerely express themselves in

16:30

service of marketing something, but

16:32

it's done in a way where like a we can say

16:34

who we choose to advertise with, and then on top

16:36

of that when we do, like we're giving a great endorsement

16:39

because we want to work with them. It makes

16:41

for like really fun adreads, and I think our listeners

16:43

also love that because we get to be funny and it's

16:45

not like a very straightforward ad read.

16:47

It's very much in the personality of the show.

16:49

And so we get a lot of people who are like still

16:51

talk about old ads we've done, like

16:53

for the Economists or like Spotify,

16:55

and they're like, do you have that recorded somewhere And

16:58

we're like, no, that was just for a very brief window,

17:00

but maybe we can look yeah,

17:03

exactly.

17:04

I think some of the Ron Burgundy ad reads

17:06

for Sharman toilet Paper are some

17:08

of the single best pieces of content ever

17:11

made by humans.

17:12

So good example.

17:13

But look, it's not every day that you can say

17:15

like I'm making a great ad product for brands,

17:17

I'm also making a show that is just

17:20

killer.

17:20

So we are at time.

17:22

I could genuinely talk to you guys

17:24

for another half hour, very easily, but

17:27

I want to respect all our viewers times too. Jack

17:30

Miles, thank you guys so much for

17:32

taking a half hour to talk to us.

17:34

I really do appreciate it.

17:35

It's one thing to launch a great comedy

17:37

podcast. You guys have done that, but I think it's

17:39

another thing to give something to listeners

17:41

that's truly.

17:42

Thoughtful and meaningful through a comedic lens.

17:45

Usually in a year like this, it's actually content

17:47

we need, and so I really do deeply appreciate

17:50

it.

17:50

And thank you guys for joining today. Thanks

17:52

con thank having us. Everybody. Stay

17:54

safe. We will see you next Thursday.

17:56

Take care, guys, do

18:01

know, n I

18:03

don't know.